Potassium Persulfate → 4-Bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone

HRID 363789

반응식

HRID 363789 반응식
[Br:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:14].[K+].[K+]>O.C(#N)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[C:7]2[C:8](=[O:14])[C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 24412Potassium PersulfateHCID 539891274-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran

생성물 1

HCID 543779064-Bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone수율 67%

시약·촉매·용매 3

HCID 24463Copper sulfate pentahydrate촉매HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

Under a nitrogen atmosphere, a stirred solution of 3.0 grams (0.013 mole) 4-bromo-2,3-dihydro-2,2-dimethylbenzofuran, 10.7 grams (0.039 mole) of potassium persulfate, and 3.3 grams (0.013 mole) of copper(II) sulfate pentahydrate in 30 mL of water and 30 mL of acetonitrile was heated at reflux for one hour. After this time the reaction mixture was poured into 200 mL of water. The mixture was then extracted with one 200 mL portion of diethyl ether. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using 1:1 petroleum ether and methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 2.1 grams of 4-bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone. The NMR spectrum was consistent with the proposed structure. Steps A through C were repeated.

후처리

  1. temperatureat reflux for one hour
  2. extractionThe mixture was then extracted with one 200 mL portion of diethyl ether
  3. dry with materialThe extract was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  6. washElution
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5a9cfecf7cdd4829b90d7bb4c1e90f3e
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874579

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